US7534749B2 - Lube base oil and lubricating oil composition - Google Patents

Lube base oil and lubricating oil composition Download PDF

Info

Publication number
US7534749B2
US7534749B2 US10/540,569 US54056905A US7534749B2 US 7534749 B2 US7534749 B2 US 7534749B2 US 54056905 A US54056905 A US 54056905A US 7534749 B2 US7534749 B2 US 7534749B2
Authority
US
United States
Prior art keywords
base oil
lube base
group
oil
exhibits
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related, expires
Application number
US10/540,569
Other languages
English (en)
Other versions
US20060166844A1 (en
Inventor
Tatsuya Egawa
Toshiyuki Tsubouchi
Yoshio Hironaka
Masahiro Yoshimoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Idemitsu Kosan Co Ltd
Original Assignee
Idemitsu Kosan Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd
Assigned to IDEMITSU KOSAN CO., LTD. reassignment IDEMITSU KOSAN CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: EGAWA, TATSUYA, HIRONAKA, YOSHIO, TSUBOUCHI, TOSHIYUKI, YOSHIMOTO, MASAHIRO (DECEASED), YOSHIMOTO, JUNKO (LEGAL REPRESENTATIVE)
Publication of US20060166844A1 publication Critical patent/US20060166844A1/en
Application granted granted Critical
Publication of US7534749B2 publication Critical patent/US7534749B2/en
Adjusted expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/02—Specified values of viscosity or viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/18—Ethers, e.g. epoxides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/34—Esters of monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/1213—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/065—Saturated Compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/071—Branched chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/36—Seal compatibility, e.g. with rubber
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/74—Noack Volatility
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present invention relates to a lube base oil and to a lubricating oil composition. More particularly, the invention relates to a lube base oil and to a lubricating oil composition, which realize reduction of evaporation loss despite being of low viscosity and excellent compatibility with organic materials.
  • Ester-based oil compositions are known to be lubricating oil compositions which have low viscosity and exhibit low evaporation loss. However, these compositions have high polarity and have adverse effects on organic materials, such as inducing swelling. For example, when such an ester-based oil composition is used in an engine oil, problematic swelling of a sealing material and-other materials made of rubber occurs. When the composition is used in an oil for hydraulic bearings or oilless bearings, plastic materials are adversely affected. In addition, these ester-based oil compositions have poor solubility with respect to additives, which is also problematic.
  • Silicone oil serves as a lube base oil which has low viscosity and exhibits low evaporation loss, but has problems of poor lubricity and high cost.
  • Poly( ⁇ -olefin) is known to be a base oil which has low viscosity and exhibits low evaporation loss.
  • a poly( ⁇ -olefin) categorized in a viscosity grade of 4 mm 2 /s (100° C.) is unsatisfactory in terms of low viscosity
  • a poly( ⁇ -olefin) categorized in a viscosity grade of 2 mm 2 /s (100° C.) is unsatisfactory in terms of low volatility.
  • Japanese Patent Application Laid-Open (kokai) No. 10-324883 discloses a lube base oil which contain a compound having an ether bond and exhibits a viscosity index and a pour point falling within a limited range.
  • a lube base oil having lower viscosity and exhibiting small evaporation loss is demanded.
  • an object of the present invention is to provide a lube base oil and lubricating oil composition which realize reduction of evaporation loss despite being of low viscosity and excellent compatibility with organic materials.
  • Another object of the invention is to provide a lubricating oil composition containing the lube base oil.
  • the present inventors have carried out extensive studies in order to attain the aforementioned objects, and have found that the aforementioned objects can be attained through causing kinematic viscosity, evaporation loss and/or flash point, and aniline point of the base oil to fall within specific corresponding ranges.
  • the present invention has been accomplished on the basis of this finding.
  • the present invention provides a lube base oil other than silicone oil having a kinematic viscosity of 12 mm 2 /s or below at 40° C., exhibiting, in Noack test (250° C., 1 hr), an evaporation loss of 30 mass % or below and/or a flash point of 200° C. or higher, and exhibiting an aniline point of 60° C. or higher.
  • a lubricating oil composition comprising the lube base oil mixed with at least one additive selected from the group consisting of an antioxidant, a viscosity index improver, a detergent dispersant, a friction reducing agent, a metal inactivator, a pour point depressant, an abrasion resisting agent, a defoamer, and an extreme-pressure additive.
  • FIG. 1 shows a 1 H-NMR spectrum of the compound produced in Production Example 1.
  • FIG. 2 shows a 13 C-NMR spectrum of the compound produced in Production Example 1.
  • the lube base oil of the present invention must satisfy at least the following conditions (i) to (iii).
  • the lube base oil of the present invention has (i) a kinematic viscosity at 40° C. of 12 mm 2 /s or below, preferably 11 mm 2 /s or below, more preferably 10 mm 2 /s or below.
  • a kinematic viscosity at 40° C. of 12 mm 2 /s or below, preferably 11 mm 2 /s or below, more preferably 10 mm 2 /s or below.
  • the lube base oil of the present invention exhibits (ii) in Noack test (250° C., 1 hr), an evaporation loss of 30 mass % or below and/or a flash point of 200° C. or higher (i.e., fourth class petroleum).
  • the evaporation loss is preferably 25 mass % or below, more preferably 15 mass % or below.
  • the flash point is preferably 210° C. or higher, more preferably 220° C. or higher.
  • the flash point is lower than 200° C., the amount of base oil lost through evaporation during use thereof increases, thereby shortening the service life of the lube oil.
  • the Noack test fails to determine actual volatility due to effects such as oxidation-induced decomposition. Such effects may be suppressed through addition of an anti-oxidant or a similar substance.
  • volatility of the base oil is determined through employment of the Noack test results and flash point in combination.
  • the lube base oil of the present invention exhibits (iii) an aniline point of 60° C. or higher, preferably 80° C. or higher, more preferably 90 to 110° C.
  • an aniline point of 60° C. or higher, preferably 80° C. or higher, more preferably 90 to 110° C.
  • compatibility with organic materials is impaired. That is, swelling of organic materials (e.g., plastics and rubber) used in an apparatus occurs.
  • organic materials may be shrunk.
  • the lube base oil of the present invention preferably has a viscosity index, as measured in accordance with JIS K 2283, of 100 or higher, more preferably 120 or higher.
  • the lube base oil of the present invention preferably has a pour point, as measured in accordance with JIS K 2265, of ⁇ 15° C. or lower, more preferably ⁇ 25° C. or lower.
  • the lube base oil of the present invention which satisfies the above conditions, preferably contains a compound formed of carbon atom, hydrogen atom, and oxygen atom (hereinafter referred to as “oxygen-containing compound”).
  • oxygen-containing compound a compound formed of carbon atom, hydrogen atom, and oxygen atom
  • a compound having an ether structure, an ester structure, or a carbonate structure is preferred.
  • an ether compound is particularly preferred.
  • the ether compound is preferably any of the compounds represented by the following formula, or a mixture thereof.
  • R 1 and R 5 each independently represents hydrogen atom, an alkyl group having 1 to 24 carbon atoms, a phenyl group, or an alkylaryl group having 7 to 24 carbon atoms;
  • R 2 , R 3 , and R 4 each independently represents an alkylene group having 2 to 18 carbon atoms; each of a, b, and c is 0 to 8 (preferably 0 to 5) as an averaged value; the sum of a to c is 0 to 8 (preferably 0 to 5); and the units (R 2 —O), (R 3 —O), and (R 4 —O) may be identical to or different from one another.
  • the alkyl group represented by R 1 or R 5 may be linear, branched, or cyclic.
  • Examples of the alkyl group include methyl group, ethyl group, propyl group, butyl group, hexyl group, 2-ethylhexyl group, 3,5,5-trimethylhexyl group, heptyl group, octyl group, 3,7-dimethyloctyl group, nonyl group, 2-pentylnonyl group, decyl group, 2-octylundecanyl group, dodecyl group, cyclopentyl group, and cyclohexyl group.
  • 2-ethylhexyl group, 3,5,5-trimethylhexyl group, octyl group, 3,7-dimethyloctyl group, nonyl group, 2-pentylnonyl group, decyl group, and 2-octylundecanyl group are particularly preferred.
  • Examples of the alkylaryl group represented by R 1 or R 5 include alkylphenyl group and alkylnaphthyl group.
  • Exampled of the alkyl moiety of the alkylaryl group include the groups described above. Among them, octyl group, decyl group, and dodecyl group are particularly preferred.
  • the alkylene group represented by R 2 , R 3 , or R 4 may be linear, branched, or cyclic.
  • Examples of the alkylene group include ethylene group, propylene group, butylene group, hexylene group, nonylene group, decylene group, dodecylene group, cyclopentylene group, and cyclohexylene group. Of these, ethylene group, propylene group, butylene group, hexylene group, nonylene group, and decylene group are particularly preferred.
  • the lube base oil of the present invention may contain, in addition to the oxygen-containing compound, a hydrocarbon compound, so long as the lube base oil satisfies the above-mentioned conditions (i) to (iii).
  • hydrocarbon compound No particular limitation is imposed on the hydrocarbon compound to be mixed with the oxygen-containing compound, so long as the hydrocarbon compound does not impair the effects of the lube base oil of the present invention.
  • the hydrocarbon compound include mineral oils (e.g., 80 neutral mineral oils), poly( ⁇ -olefin) (e.g., viscosity grade 4 mm 2 /s or 8 mm 2 /s (100° C.)), ethylene-propylene copolymers, and alkylbenzenes (e.g., propylbenzene and butylbenzene). Of these, poly( ⁇ -olefin) is preferred.
  • the lube base oil of the present invention excludes silicone oil.
  • the reason for exclusion is that, even though silicon oil satisfies the aforementioned requirements, silicon oil exhibits poor lubricity and is expensive.
  • the lube base oil of the present invention may be blended with a variety of additives in accordance with uses including engine use, thereby providing a lubricating oil composition.
  • the lube base oil of the present invention per se may serve as a lube oil.
  • the lube base oil is blended with any of the following additives, to thereby form a lubricating oil composition, and the composition is employed as a lube oil suited for any of the uses.
  • any known additives may be used as the aforementioned additives.
  • the antioxidant include amine compounds such as alkylated dipheylamine and phenyl- ⁇ -naphthylamine and phenol compounds such as 2,6-di-tert-butylphenol, 4,4′-methylenebis (2,6-di-tert-butylphenol).
  • the viscosity index improver include poly(methyl methacrylate)-based, polyisobutylen-based, ethylene-propylene copolymer-based, styrene-isoprene copolymer-based, and styrene-butadiene hydrogenated copolymer-based improvers.
  • detergent dispersant examples include metallic detergents such as alkaline earth metal sulfonates, alkaline earth metal phenates, alkaline earth metal salicylates, and alkaline earth metal phosphonates and ash-free dispersants such as alkenylsuccinimides, benzylamines, alkyl-polyamines, and alkenylsticcinic esters.
  • the friction reducing agent examples include aliphatic alcohols, fatty acids, fatty acid esters, aliphatic amines, aliphatic amine salts, aliphatic acid amides.
  • metal inactivator examples include benzotroazole, thiadiazole, and alkenylsuccinic acid esters.
  • Examples of the pour point depressant include polyalkyl metacrylate, and polyalkylstyrene.
  • examples of the, antiwear agent include organic molybdenum compounds such as MoDTP and MODTC; organic zinc compounds such as ZnDTP; organic boron compounds such as alkylmercaptyl borate, and solid lubricant antiwear agents such as graphite, molybdenum disulfide, antimony sulfide, boron compounds, and polytetrafluoroethylene.
  • Examples of the defoamer include dimethylpolysiloxane and polyacrylates.
  • examples of the extreme-pressure additive include sulfurized fats and oils, diphenyl sulfide, methyl trichlorostearate, and chlorinated naphthalene.
  • the lube base oil of the present invention is applicable to a variety of uses. Examples include internal combustion engines, hydraulic oil, automatic transmission fluid, manual transmission fluid, bumper oil, gear oil, hydraulic bearing oil, roll bearing oil, oil retaining bearing oil, sliding surface oil, and refrigerator oil.
  • Viscosity index was measured in accordance with JIS K 2283.
  • Aniline point was measured in accordance with JIS K 2256.
  • Evaporation loss was measured in accordance with ASTM D 5800 (Noack test: 250° C., 1 hr).
  • 2-Octyl-1-dodecanol 300 g
  • 1-bromooctane 300 g
  • tetrabutylammonium bromide 30 g
  • an aqueous sodium hydroxide solution 500 g
  • sodium hydroxide 150 g
  • water 350 g
  • reaction mixture was transferred to a separating funnel, and the aqueous layer was separated through filtration. The remaining organic layer was washed five times with water (500 mL). The organic layer was distilled under reduced pressure, to thereby separate a compound.
  • the purity of the compound was determined by means of a gas chromatography analyzer (analyzer: Model Hitachi 263-70, column: OV-1 packed column (product of GL Science Inc.) (2 m)) to be 99% or higher (as calculated based on peak area).
  • the compound was identified as an ether compound having a structure represented by the following formula by means of nuclear magnetic resonance apparatus ( 1 H-NMR, 13 C-NMR: GSX400, product of JOEL Ltd.).
  • FIGS. 1 and 2 show the obtained 1 H-NMR and 13 C-NMR spectra, respectively.
  • 2-Hexyl-1-decanol 121 g
  • diethylaniline 61 g
  • diethyl ether 150 mL
  • Octanoyl chloride 82 g was slowly added dropwise to the mixture under stirring.
  • the ether layer was separated, washed four times with 10% sulfuric acid (100 mL), washed with water, and dried over Glauber's salt, followed by removing ether.
  • the organic layer was distilled under reduced pressure, to thereby yield 82 g of a distilled product.
  • the structure of the product was analyzed in a manner similar to that employed in Production Example 1, thereby identifying the product to be an ether compound having a structure represented by the following formula.
  • the organic layer was distilled under reduced pressure, to thereby yield 48 q of a distilled product.
  • the structure of the product was analyzed in a manner similar to that employed in Production Example 1, thereby identifying the product to be an ether compound having a structure represented by the following formula.
  • the compound obtained in Production Example 7 was mixed with poly( ⁇ -olefin) (tradename: HITEC 164, product of ETHYL) at a ratio by mass of 1:1.
  • the mixture was measured in terms of the characteristics (1) to (6) mentioned above. The results are shown in Table 1.
  • the compound obtained in Production Example 8 was mixed with poly( ⁇ -olefin) (tradename: HITEC 164, product of ETHYL) at a ratio by mass of 2:3.
  • the mixture was measured in terms of the characteristics (1) to (6) mentioned above. The results are shown in Table 1.
  • Poly( ⁇ -olefin) (tradename: HITEC 164, product of ETHYL) was measured in terms of the characteristics (1) to (6) mentioned above. The results are shown in Table 1.
  • the lube base oil and the lubricating oil composition of the present invention attain excellent fuel-cost-saving effect by virtue of low viscosity, a long service life by virtue of a small evaporation loss, and excellent compatibility with organic materials.
  • the lube base oil and the lubricating oil composition are useful for engine oil for use in internal combustion engines, and lubricating oils such as bearing oils.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
US10/540,569 2002-12-24 2003-12-24 Lube base oil and lubricating oil composition Expired - Fee Related US7534749B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2002372397 2002-12-24
JP2002-372397 2002-12-24
PCT/JP2003/016597 WO2004058928A1 (ja) 2002-12-24 2003-12-24 潤滑油基油及び潤滑油組成物

Publications (2)

Publication Number Publication Date
US20060166844A1 US20060166844A1 (en) 2006-07-27
US7534749B2 true US7534749B2 (en) 2009-05-19

Family

ID=32677228

Family Applications (1)

Application Number Title Priority Date Filing Date
US10/540,569 Expired - Fee Related US7534749B2 (en) 2002-12-24 2003-12-24 Lube base oil and lubricating oil composition

Country Status (4)

Country Link
US (1) US7534749B2 (de)
EP (1) EP1577371A4 (de)
JP (1) JP4769463B2 (de)
WO (1) WO2004058928A1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090116771A1 (en) * 2005-11-15 2009-05-07 Idemitsu Kosan Co. Ltd Lubricant composition, bearing oil and bearing using same
US20110152143A1 (en) * 2008-06-11 2011-06-23 Idemitsu Kosan Co., Ltd. Lubricating oil composition

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4563082B2 (ja) 2004-06-03 2010-10-13 出光興産株式会社 潤滑油基油及び潤滑油組成物
JPWO2006025253A1 (ja) * 2004-08-30 2008-05-08 出光興産株式会社 流体軸受用潤滑油組成物
KR100865207B1 (ko) * 2004-12-08 2008-10-23 파나소닉 주식회사 냉매 압축기
JP5249492B2 (ja) * 2005-08-31 2013-07-31 出光興産株式会社 油圧作動油組成物
JP5122740B2 (ja) * 2005-11-15 2013-01-16 出光興産株式会社 冷凍機油組成物
JP4871606B2 (ja) * 2006-02-03 2012-02-08 出光興産株式会社 ポリエーテル化合物及びそれを含む潤滑油用基油と潤滑油組成物
JP5101877B2 (ja) * 2006-12-28 2012-12-19 Ｊｘ日鉱日石エネルギー株式会社 緩衝器用油圧作動油組成物
JP5231053B2 (ja) * 2008-03-14 2013-07-10 Ｊｘ日鉱日石エネルギー株式会社 潤滑油組成物
US9365789B2 (en) 2012-12-27 2016-06-14 Idemitsu Kosan Co., Ltd. Dialkyl ether, and lubricant base oil and lubricating oil composition containing the same
US10323204B2 (en) * 2013-10-25 2019-06-18 Exxonmobil Research And Engineering Company Low viscosity, low volatility lubricating oil basestocks
US10323203B2 (en) * 2013-10-25 2019-06-18 Exxonmobil Research And Engineering Company Low viscosity, low volatility lubricating oil basestocks
JP6231877B2 (ja) * 2013-12-27 2017-11-15 出光興産株式会社 ジアルキルエーテルを含む潤滑油基油
JP6204241B2 (ja) * 2014-03-27 2017-09-27 出光興産株式会社 駆動系用潤滑油基油及び駆動系用潤滑油組成物
JP6259728B2 (ja) * 2014-06-30 2018-01-10 出光興産株式会社 潤滑油組成物
KR101819132B1 (ko) 2015-02-09 2018-01-16 가부시키가이샤 모레스코 윤활제 조성물과 그 이용 및 지방족 에테르 화합물
AU2016280054B2 (en) * 2015-06-18 2020-05-07 Castrol Limited Ether compounds and related compositions
SG11201802634VA (en) * 2015-11-13 2018-05-30 Exxonmobil Res And Enginerring Company Low viscosity low volatility lubricating oil base stocks and processes for preparing same
WO2017083066A1 (en) * 2015-11-13 2017-05-18 Exxonmobil Research And Engineering Company Low viscosity low volatility lubricating oil base stocks and processes for preparing same
EP4095220B1 (de) * 2016-12-16 2024-07-31 Castrol Limited Etherbasierte schmiermittelzusammensetzungen, verfahren und verwendungen
US20200115651A1 (en) * 2016-12-16 2020-04-16 Castrol Limited Ether-Based Lubricant Compositions, Methods and Uses

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2605292A (en) 1947-05-09 1952-07-29 Celanese Corp Preparation of butylene glycol ethers
EP0170076A1 (de) 1984-07-05 1986-02-05 BASF Aktiengesellschaft Wärmeträgerflüssigkeiten
US4790957A (en) * 1986-10-18 1988-12-13 Basf Aktiengesellschaft Polycarboxylic acid esters and lubricants containing these esters
JPH02300293A (ja) 1989-05-16 1990-12-12 Nippon Kouyu:Kk 低温流動性、耐プラスチック性を向上したグリース組成物
JPH08259974A (ja) 1994-12-14 1996-10-08 Idemitsu Kosan Co Ltd 潤滑油基油及びその製造方法
JPH09100480A (ja) 1995-10-05 1997-04-15 Idemitsu Kosan Co Ltd 軽質潤滑油基油及びその製造方法
JPH10324883A (ja) 1997-05-27 1998-12-08 Idemitsu Kosan Co Ltd 潤滑油基油
JP2000044971A (ja) 1998-07-28 2000-02-15 Idemitsu Kosan Co Ltd 緩衝器用潤滑油組成物
EP0992570A2 (de) 1998-10-09 2000-04-12 Tonen Corporation Hydraulisches Öl für Stossdämpfer
JP2002146381A (ja) 2000-11-17 2002-05-22 Cosmo Sekiyu Lubricants Kk 軸受用潤滑油
JP2004051720A (ja) 2002-07-18 2004-02-19 Idemitsu Kosan Co Ltd 液体潤滑剤、潤滑油組成物及び軸受油

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4214653A1 (de) * 1992-05-02 1993-11-04 Henkel Kgaa Motorengrundoele mit verbesserter dichtungsvertraeglichkeit

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2605292A (en) 1947-05-09 1952-07-29 Celanese Corp Preparation of butylene glycol ethers
EP0170076A1 (de) 1984-07-05 1986-02-05 BASF Aktiengesellschaft Wärmeträgerflüssigkeiten
US4790957A (en) * 1986-10-18 1988-12-13 Basf Aktiengesellschaft Polycarboxylic acid esters and lubricants containing these esters
JPH02300293A (ja) 1989-05-16 1990-12-12 Nippon Kouyu:Kk 低温流動性、耐プラスチック性を向上したグリース組成物
JPH08259974A (ja) 1994-12-14 1996-10-08 Idemitsu Kosan Co Ltd 潤滑油基油及びその製造方法
JPH09100480A (ja) 1995-10-05 1997-04-15 Idemitsu Kosan Co Ltd 軽質潤滑油基油及びその製造方法
JPH10324883A (ja) 1997-05-27 1998-12-08 Idemitsu Kosan Co Ltd 潤滑油基油
JP2000044971A (ja) 1998-07-28 2000-02-15 Idemitsu Kosan Co Ltd 緩衝器用潤滑油組成物
EP0992570A2 (de) 1998-10-09 2000-04-12 Tonen Corporation Hydraulisches Öl für Stossdämpfer
JP2002146381A (ja) 2000-11-17 2002-05-22 Cosmo Sekiyu Lubricants Kk 軸受用潤滑油
JP2004051720A (ja) 2002-07-18 2004-02-19 Idemitsu Kosan Co Ltd 液体潤滑剤、潤滑油組成物及び軸受油

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090116771A1 (en) * 2005-11-15 2009-05-07 Idemitsu Kosan Co. Ltd Lubricant composition, bearing oil and bearing using same
US20110152143A1 (en) * 2008-06-11 2011-06-23 Idemitsu Kosan Co., Ltd. Lubricating oil composition
US8962540B2 (en) * 2008-06-11 2015-02-24 Idemitsu Kosan Co., Ltd. Lubricating oil composition

Also Published As

Publication number Publication date
JP4769463B2 (ja) 2011-09-07
EP1577371A4 (de) 2008-11-05
JPWO2004058928A1 (ja) 2006-04-27
EP1577371A1 (de) 2005-09-21
WO2004058928A1 (ja) 2004-07-15
US20060166844A1 (en) 2006-07-27

Similar Documents

Publication Publication Date Title
US7534749B2 (en) Lube base oil and lubricating oil composition
JPWO2011118708A1 (ja) 潤滑油添加剤及びそれを含有する潤滑油組成物
KR101301343B1 (ko) 윤활유 조성물
JP4563082B2 (ja) 潤滑油基油及び潤滑油組成物
JP5438773B2 (ja) 炭化水素アミンと環状カーボネートとから誘導した摩擦調整剤及び／又は摩耗防止剤
US20060148663A1 (en) Additives for lubricating oils and fuel oils, lubricating oil compositions, and fuel oil compositions
JP4334986B2 (ja) エンジン油組成物
JP4981240B2 (ja) 潤滑油用及び燃料油用添加剤、並びに潤滑油組成物及び燃料油組成物
KR101216823B1 (ko) 윤활유용 및 연료유용 첨가제, 윤활유 조성물 및 연료유조성물
JP2001049280A (ja) エンジン油
JP4981241B2 (ja) 潤滑油用及び燃料油用添加剤、並びに潤滑油組成物及び燃料油組成物
US11739281B2 (en) Use of a lubricant composition for transmission
JP2014125630A (ja) クロスヘッド型ディーゼル機関用システム潤滑油組成物
JPH07150170A (ja) 潤滑油組成物
JP2014024827A (ja) 新規フェノール系化合物
JP5112402B2 (ja) 潤滑油用及び燃料油用添加剤、並びに潤滑油組成物及び燃料油組成物
JP7641869B2 (ja) 潤滑油組成物
JP7611107B2 (ja) 潤滑油組成物
US20250257279A1 (en) Lubricating oil composition for internal combustion engine
JP5097178B2 (ja) 潤滑油用及び燃料油用添加剤、並びに潤滑油組成物及び燃料油組成物
JP5546398B2 (ja) 潤滑油用酸化防止剤及びそれを含有する潤滑油組成物
JPH08209173A (ja) 潤滑油組成物
JP2009084263A (ja) メルカプトアルカンカルボン酸エステル亜鉛塩およびその製造方法、潤滑油添加剤、および潤滑油組成物

Legal Events

Date Code Title Description
AS Assignment

Owner name: IDEMITSU KOSAN CO., LTD., JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:EGAWA, TATSUYA;TSUBOUCHI, TOSHIYUKI;YOSHIMOTO, MASAHIRO (DECEASED), YOSHIMOTO, JUNKO (LEGAL REPRESENTATIVE);AND OTHERS;REEL/FRAME:017391/0646

Effective date: 20050624

STCF Information on status: patent grant

Free format text: PATENTED CASE

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FPAY Fee payment

Year of fee payment: 4

FPAY Fee payment

Year of fee payment: 8

FEPP Fee payment procedure

Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

LAPS Lapse for failure to pay maintenance fees

Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362

FP Lapsed due to failure to pay maintenance fee

Effective date: 20210519